


The Kanto Region Master

by DraceDomino



Category: Pocket Monsters | Pokemon (Anime), Pocket Monsters | Pokemon - All Media Types
Genre: Aged-Up Character(s), Breeding, F/M, Forest Sex, Friends to Lovers, Nudity, Oral Sex, Public Nudity, Rough Sex, Vaginal Sex
Language: English
Status: Completed
Published: 2018-05-23
Updated: 2018-08-09
Packaged: 2019-05-10 10:13:34
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 9,650
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14735027
Author URL: https://archiveofourown.org/users/DraceDomino/pseuds/DraceDomino
Summary: Ash Ketchum became the most decorated Pokemon master there was...and then mysterious went to live in the woods by himself. Years later Serena finally decides to track down her old friend to see if the same spark remains - and what she finds leaves her shocked at how Ash lives his life, and completely enchanted that she could be a part of it, too!





	1. Chapter 1

The Kanto Region Master  
-by Drace Domino

It really brought back memories, heading through the woods with little more than a few Poké balls at her side. As Serena worked her way deeper and deeper into the wilderness, it was impossible to not dwell on those fond days, knowing in her heart that they were some of the best she ever had. It had been a few years since she said farewell to Ash and the two went their own separate ways, but all she ever had to do in order to remember him was hop into the woods and look for new and fascinating Pokémon to battle and befriend.

At least, now that the news stopped mentioning him on a nearly weekly basis. For a while Ash Ketchum was one of the biggest names there was, gaining honor after honor and having accolades piled atop him. Tournament wins came naturally to him even when he was a child, and the rare defeats had always led to him improving his skill and becoming a better trainer. By the time Ash had hit twenty he was easily one of the greatest trainers in the whole world, which naturally led to a great swell of pride within those that knew him when he was young.

Serena among them, who hadn’t seen her old friend in far, far too many years. It was the reason she was moving through the woods that day, clutching her map in both hands as she headed steadily towards the mountain peak in the distance. Delia didn’t know her son’s actual location when Serena had pressed her, but the general consensus was that Ash had left for the deep wilderness of Kanto. A wilderness that Serena was creeping through carefully, in order to cause as little a disturbance as possible.

“Here’s got to be around here somewhere.” Serena mused to herself as she knelt down, inspecting yet another set of tracks even as the sun started to go down. It’d be evening soon before too long, but she pushed that concern away as her fingers moved over the footprint of what had to be a Sandslash. “Ash...I just know you’re nearby.”

The footprint, like all those that Serena had seen for the past few hours, was bigger than normal for a Pokémon of that type. The deeper she went into the Kanto region it seemed like the more the local Pokémon thrived, and it couldn’t purely be because they were away from the bustling cities. Someone was taking particularly good care of the Pokémon nearby, and it only proved to the young woman all the more that her old friend was near. It was a comforting thought to know that even when Ash turned his back on the rest of the world and went into seclusion he didn’t lose his fondness for the wonderful creatures that improved everyone’s lives. No matter the awards he won or the fame he had reached, Ash Ketchum was still the same sweet boy from Palette Town that had earned a crush from Serena so long ago.

As the girl continued along, soon the setting sun proved that it wouldn’t allow her trip to go much further. The deep woods of Kanto were a dangerous trek even under ideal conditions, but soon the nocturnal Pokémon would be out and about making it far more likely to stumble across them and find herself in trouble. After all, it’d be a poor way to reunite with Ash if the first time he saw her was in the midst of defending herself in a wild Pokémon battle. By the time the sun was very nearly down and the forest completely dark, the girl had found herself a spot at the base of a tree with a thick canopy, sitting cross-legged by the light of a portable lantern and quietly munching on her rations.

Once more, memories of the old days flooded back to her. The fun and joy of sitting around a campfire with all her friends, the looks she used to steal of Ash when his attention was turned elsewhere, the feeling of camaraderie and friendship shared between people and Pokémon alike. Rations tasted a whole lot better than they did all those years ago, but...it was a poor consolation considering she was eating them by herself now.

“...maybe I’ll find him tomorrow.” Serena finally sighed, and moved a hand up to grasp her fashionable pink cap. She was older now, sure, but she’d never give up on her cute, chic style! As she tossed her cap to the side and leaned back against the tree, Serena gazed once more to the stars above and let memories overtake her. By the time she fell asleep the forest was quiet and dark, her lantern dimming, and thoughts of her old friend were still teasing along her mind.

She didn’t even know what she’d say to him upon seeing Ash once again, all she knew was that a deep, intimate part of her desperately wished to connect with her old, dear friend once more.

***

When Serena woke up in the morning, it was to the savory yet slightly familiar smell of breakfast cooking. The woman’s eyes fluttered open and a slow stretch rolled through her; one that almost instantly reminded her that she had fallen asleep while fully dressed in her clothes from the previous day. She hadn’t been quite so freewheeling as to travel around in a skirt and stockings like she did in the old days, but her slightly baggy cargo pants and thick boots weren’t exactly the most comfortable thing to doze in. She was still glancing down at herself and blinking the sleep away from her eyes when she took in another breath, and once more found a delicious aroma in the air that triggered her nostalgic memories anew.

And when she looked up, she saw a tiny fire nearby with a slowly rolling pot of stew resting overtop it. The same sort of makeshift campfire they used to put together in the old days was waiting for her, and nearby a pair of metal bowls waited for breakfast to be spooned out. As she suddenly crawled to her hands and knees and approached it, it became quite evident that it was a meal she had enjoyed before. A few vegetables, a few spices, a few berries...something that was common for Pokémon trainers out in the field, and a dish that Serena had eaten her fair share of in the past. Just as her belly was starting to rumble at the thought of diving in and taking a bowl of the suddenly appearing stew, a voice filled the air to finally greet her to the waking world.

“I didn’t think I’d ever see you again, Serena.” She knew from the first word that it was Ash - his youthful tone was almost the exact same after all these years. It was rather early in the morning for the girl to handle such sudden jubilation, and she was still batting the sleep from her eyes and looking around eagerly as his voice filled the tiny clearing around them. “What brings you all the way out here?”

“Y-You did!” Serena stammered, and moved a hand up to rub quickly at her eyes. Her head darted in the direction she heard her old friend’s voice, and when she opened them her heart was racing at the notion of seeing his face in person after all this time. “Oh, Ash! I’m so glad I finally found yo-whaaaaat?!”

It was good to see Ash Ketchum again. It was another thing to see him standing at the edge of the clearing completely and totally naked.

Serena more or less froze in place in that moment; one eye half-closing and giving a few twitches of surprise as she continued to stare. It was definitely Ash all right; his face still friendly and inviting and his hair the same sort of dishevelled black mess that needed a good combing. It was impossible for her eyes to not give a long gaze at the young man’s naked frame, from his smooth shoulders leading into what had become impressive arms, and across his lap where his member hung free. During her most...private thoughts in the past few years she had wondered what Ash’s cock looked like, but never had she imagined he’d just wander up to her with it hanging out! She was still struggling to snap out of it by the time Ash spoke again, striding forward towards the campfire with an enthusiastic tone in his voice.

“I made us some breakfast, Serena!” He smiled, dropping down to a knee and taking up an empty bowl. After spooning up a serving for his old friend he eagerly handed it over to her, smiling while it was taken with a trembling, quivering hand. “Just like the old days, huh?”

Every part of her wanted to stand up and scream “You used to wear clothes in the old days,” but instead Serena merely took the bowl, nodded, and stared.

She stared for a long, long time before finally taking a bite of stew.

 

It took Serena a while to assure herself that she wasn’t having one of the strangest dreams of her life. She sat with her back to a tree as Ash was sitting cross-legged from her, his cock sticking up in a state of half-arousal and his hands at work as he ate breakfast. For every five bites of stew Ash took down Serena was lucky to manage one, and the trembling of her hand made sure that more than just a bit of it managed to splash across her chest. Ash, despite his lack of clothes, was just as friendly as ever and his tone reflected the naive charm that made him so endearing when they travelled together.

“Pikachu is going to be so happy to see you again!” He beamed, and swallowed down another mouthful of stew. “And I’ve met so many other great Pokémon to introduce you to! How are things back home? Have you talked to Clemont and Bonnie recently? How are they doing?” He barely waited a half-second for a response before asking yet another question, smiling the entire time. “Did you really come all the way out here just to see me?”

“Yes!” Serena finally blurted out, her eyes opening wide and her hand tightening around the edge of her bowl. She took a long, deep breath and forced her gaze away from Ash’s cock, as strangely hypnotic as it was to see hanging out so freely. “Ash, nobody’s heard from you in over a year. I went from seeing you on the news every week to...to nothing!” She suddenly gestured to the young man, her fingers pointing vaguely at his naked lap. “And I see you after all this time and...and you’re like this?!”

“Huh?” Ash looked up from his stew mid-bite, a piece of carrot half-clenched in his teeth. “Like wha--” The carrot dropped from his mouth right back into his bowl as he looked down, and a look of realization struck him. “Oh! Oh wow, Serena, sorry! I completely forgot! Uh...how’s this?!” A quick gesture brought his breakfast bowl down to hold it in front of his cock, which did little to hide it. It did nothing to mask the sight of his sack just underneath, or the stiff tip sticking out over the rim. As he held it there Ash gave a chuckling and apologetic look, one hand moving up to rub the back of his head. “I haven’t worn clothes in a while. It’s...easier to get used to than you think. It only took me a few weeks before I stopped missing them altogether!”

“I...I bet.” Serena merely murmured in response, and took another bite of the familiar breakfast. Once more a deep breath ran through the young woman, and her eyes remained locked on Ash’s face. Well...mostly locked. From time to time she still gazed down to steal a look at the tip of his cock, completely unobstructed by his breakfast. “Ash, it’s been years since we’ve seen each other. And I missed you. When you disappeared I...I guess I sort of thought I’d hear from you one day. I know it’s been a long time, but...I thought we...uh…” Her words quickly lost momentum as her cheeks drew a deeper and deeper blush, and she finally found herself retreating within herself. She even reached a hand out to pick up her fashionable hat, popping it back on her head and pulling down the front to hide her face as best as she was able. From a few feet away Ash tilted his head and gave his friend a sympathetic look, and rolled his shoulders as he responded.

“Gee Serena, I didn’t mean anything by it.” The young man finally smiled. “I just...needed to get away from everything. I never became a Pokémon trainer to be on the news or to be interviewed by celebrities. I did it because I love Pokémon. And I was afraid if I kept going like I was that it’d stop being about them.” He looked from side to side at the wooded area around them, smiling. From the rustling in the trees thanks to the plump and healthy Caterpies to the cries of distant Spearows, the place was full of life. Life that he had helped nurture in the past long year. “I guess I loved it out here so much that I just sort of forgot about everything back home.”

“...and clothes.”

“And clothes.” Ash laughed in response to his friend, and finally slinked a little closer. It was the most intimate the two friends had ever been, or at the very least it was the most Ash had ever been exposed. When he drew in close to Serena and finally set his stew aside, his member was fully exposed and revealed once more to her curious gaze. Without any intention of hiding it, Ash reached his hand out and closed it around Serena’s knee, fingers tightening fondly and giving her a tiny squeeze. When he spoke again he offered her a look of trust and friendship that she remembered well - a look that had always made her a little weak when they were on their adventures in the past. “You came all this way. Maybe you’d like to try it?”

Serena blinked, her cheeks darkening once more at the offer. Generally speaking, stripping down because a naked man in the woods invited her to do so wasn’t something Serena ever would’ve considered doing. But...it was Ash, and she had indeed come a long way to see him.

“Back together for a half hour, and you already have me doing something crazy.” Serena murmured, and moved her hands down to the clasp of her belt. Despite her words, her tone was charmed, pleasant, and adoring. “...I’ve really missed you, Ash.”

***

It was shocking to Serena how quickly things escalated once her clothes were off. The young lady had stood up to join Ash in his freewheeling lifestyle, stripping out of her pants and even bashfully allowing her panties to join them at her ankles. She tried to put Ash’s gaze out of her mind as she continued that morning, lifting her shirt up and over her head and slinking out of her bra in similar swift fashion. Before long the only thing she was wearing was her fashionable pink pillbox hat and a blush that started at her cheeks before travelling all the way down to her chest. Every modest part of her wanted to cover up the sight of her full breasts and well-tended nethers, and once or twice she even let her hand drift before her lap or across her nipples in a failed attempt to hide them. Ultimately; though, she knew that trying to keep herself under wraps was pointless. And besides...a part of her had always wanted Ash to see her in such a state. By the time she was finished casting aside her clothes she turned to face him full on, stretching her hands to the sides and taking a long, deep breath while the outside air of the woods washed over her.

“So...here I am.” Serena finally spoke, her blush still present upon her cheeks. “Naked. I didn’t really think this was what it’d be like when we met again.”

“Yeah, but doesn’t it feel good?” Ash beamed, jerking himself up to his feet and facing his old friend. His cock had clearly taken notice of his friend’s nude state; sticking straight out at full attention and showing off an impressive girth. In fact, he stood so close to Serena that it even swung forward and batted against her, slapping lightly against the outside of her thigh and then resting there in an almost affectionate nuzzle. While goosebumps rolled across Serena’s flesh Ash merely observed her with a smile, and moved a hand forward to tease a finger underneath her chin and lift her eyes to meet his own. “That’s what it’s like out here. You’re free to be just you. No restrictions, no rules, and no Team Rocket.”

It was just the thing to make them both laugh, each of the friends suddenly cracking up at the thought. Instantly Serena felt herself become more relaxed, and she even moved her own hand out to touch her friend’s bare shoulder with her soft, smooth palm. Even the touch of his cock against her leg didn’t bother her; and in fact she had to fight herself from moving her hand down and exploring it a little further. For the moment, she was content to just gaze at her friend and continue this moment of exposure and intimacy.

“If they suddenly pop out of the bushes and give their speech, fair warning that I’m going to get dressed again.” Serena smiled. “But otherwise? Yeah...yeah, Ash. This is pretty nice. Thanks for sharing it with me.”

It didn’t take long after that moment, with the thoughts of Team Rocket fading and the natural comfort the two felt leftover, that Serena idly let her hand drop the rest of the way. She brought her fingers to brush along Ash’s shaft from the base, and with a still-nervous touch allowed them to explore in a sweeping motion all the way towards the tip. It was a soft motion and delicate in execution, yet when she gazed at her friend Serena found herself looking at him in an entirely new fashion. She wasn’t sure just what she had expected upon setting out on her journey: whether she’d find Ash to be bitter and jaded at the civilized world, if he’d be the enthusiastic youngster at heart that he was back then, or if she’d find him some combination of the two. But as she allowed her fingers to brush across a throbbing and swelling shaft, she realized that he had become more than she would’ve guessed.

And just being near him again was enough to change her, too. The naked young woman didn’t resist as Ash let his own hand bring itself up to the edge of her pillbox hat, delicately taking it by the side and flicking it carelessly to the ground below. In a smooth motion he let his fingers dive into the girl’s light brown hair afterwards, sinking well into her locks as the two old friends finally closed the distance between each other.

Things moved quickly from there, so quick that Serena’s racing heart almost had a hard time keeping up. Before she knew it her mouth was on Ash’s own and their tongues were wrestling in a wet and hot embrace, and her fingers had fully closed around her old friend’s cock to give it a seductive squeeze. The exposure she felt out in the open only fueled a passion she had been sitting on for a while, and Ash had become uninhibited enough to act on each and every one of his impulses. The two kissed hungrily as they stood there in the clearing, and Serena melted willingly as fingers tightened around her hair and her tongue was roughly pinned to the floor of her mouth.

Ash’s cock pulsed within her hand, throbbing with nearly every heartbeat as his old friend fondled it. Serena had turned into the beautiful woman her youthful cuteness had promised, and here she was left bare and willing before him. He helped himself to grope one of her bare breasts within his palm, and as his fingers sunk in against her warm, soft flesh he relished at the moan she grumbled into the kiss. As things picked up even further Ash only barely pulled his lips away from the young woman’s, their foreheads rolling against one another as he whispered in a hushed, hungry, and heated tone.

“On your knees for me.” He urged her, just as his hands moved to Serena’s shoulders and began to nudge her down. “Show me how much you missed me.”

At that point, Serena was already far too lost to passion and the excitement of the moment to do anything but immediately comply. She nodded with a smile and with the flavor of Ash’s kiss still on her lips, dropping down so that her knees rested against the fabric of her pants that had dropped to the floor. Using that baggy fabric as a cushion, she slid her hands to Ash’s waist and brought her face just underneath the weight of his cock, resting the underside on her lips as she looked up at him. With her eyes darting across Ash’s bare chest she gave his shaft a tiny kiss, and spoke with a tender voice as her hands slid from his waist to the base of that throbbing, aroused shaft.

“I’ve wanted to do this for a long time.” Was all she purred right before going to work. Her eyes closed and she parted her lips, wrapping them around Ash’s tip so she could swirl her tongue in a wide, wet circle. Her hands closed around the base of his shaft and started to pump him slowly but steadily, using her soft touch to keep him as stiff as possible as she worked. Already his size was intimidating to the young woman, but everything else in that moment was already so overwhelming she didn’t have time to dwell on it. Who would’ve thought that so soon after reuniting with Ash that she’d be naked in the woods, readily and joyfully sucking his cock?

It was the sort of thing right out of Serena’s deepest and dirtiest fantasies that she had nurtured during their travels together; things that she dreamt about late at night and never told a soul about. And now...she was lucky enough to live those lewd, happy fantasies in person.

Serena sucked readily and greedily on Ash’s cock, taking the inches into her mouth and worshipping each one with her tongue. As the flavor of her old friend filled her mouth she only moaned all the louder around it, and more than a few times managed to take him down to the hilt. When her lips squeezed to the base of his cock and she could feel his sack pressing to her chin she did her best to hold that position, determined to prove her worth to her reclusive friend as a girl that could handle his girth. After all, a Pokémon trainer as skilled and caring as Ash deserved a girl that could deepthroat him! She was able to hold him down into her throat for a few lingering seconds each time, always improving with every attempt and showing she could learn. When her mouth pulled off of his tip ribbons of spit connected it to her lips, and they bounced and danced while she spoke with a happy gasp in her voice.

“A...Ash...it’s so good!” She beamed, stuck out her tongue wide, and gave him a slow lick from the bottom of his sack all the way up his shaft. “How am I doing?”

“You’re great, Serena!” The young man gave his old friend an enthusiastic thumbs up, and started to push his hips forward and ease his cock past her lips once more. “Keep at it, I’m almost ready to fuck you!”

Excitement crashed through Serena like a tidal wave at that announcement, her eyes going wide but her mouth gleefully returning to work. Ash certainly was a good trainer of Pokémon or people - he knew full well that the promise of getting his impressive length inside of her was just the thing Serena was craving in that moment. In order to earn it she redoubled her efforts swiftly and hungrily, sucking him down all the way to the base, fondling his sack and jerking him with warm hands, and never holding back on the warm, wet affection she could offer. Kneeling naked in the woods Serena was outright worshipping her old friend’s cock, and by the time Ash finally took a fistful of her hair and pulled her head back she was soaked beyond measure and ready to be claimed.

Ash said nothing as he pulled Serena’s head off of his cock, and continued to yank to encourage the girl to rise to her feet. On trembling legs Serena did exactly as she was positioned to, and like a Pokémon on a leash she moved into the position her friend shoved her. Before long, her hands were stinging under the bark of a tree as she leaned forward to it, bending from the waist and showing out her rump for Ash’s appraisal, approval, and eventual fucking.

“Serena, I’ve got a confession to make.” Ash finally broke the silence as he took the girl’s waist in one hand, his other moving to the base of his cock. Still dripping with Serena’s spit, he pushed it into position to line his tip up against her warm, wet folds. “I love it here, but it’s definitely missing something. I train Pokémon all day, but you know what I’d really like?”

“W...What’s that…?” Serena looked back over her shoulder, her face marked with her own spit and her hair a bit disheveled. She gave a sudden and sharp cry as Ash suddenly pushed forward, spreading her pussy around his impressive cock and fucking her almost down to the hilt. His sack slapped against the hood of her clit and her thighs spread to accommodate his cock, knees already trembling and weak and her body erupting in a moment of pleasure. Ash didn’t respond to her until his cock was already hilt-deep within her, the tip pushing to her innermost walls and the grip so tight that she could practically feel him throbbing inside of her.

“Y’know Serena, training Pokemon is great, and I’ll never give up doing it. But...that doesn’t mean I don’t wanna have kids of my own!” Ash admitted with a smirk, and intent was clear in his voice and plastered across his face. “And I’d love it if you stuck around so we could do just that!”

He didn’t give Serena a chance to respond before he started fucking her, and she certainly couldn’t find the strength to speak as soon as he started to piston his cock in and out of her tight, wet hole. Serena found herself howling in delight in the middle of the woods, as free and wild as one could imagine as her legs spread and her pussy gripped Ash’s wildly thick, hungry cock. His words still resonated deep in her mind and sent all sorts of sensations and thoughts through her, each one spinning right back to the tempest of passion that had swept her up so easily. After not seeing Ash in years she was already bending over and willing to be bred by him in incredibly rapid fashion, hardly the way she had expected things to turn out. And yet, as Ash took her waist in both his hands and continued to slam forward to crash his lap into her rear, Serena found her own voice calling out words she never would’ve imagined.

“Y-Yes Ash, fuck me! Fuck me harder, please!” Her wildest fantasies were made manifest as Ash plowed her harder and harder, leaving her pussy soaked, delighted, and craving more. Her fingers pressed into the bark of the tree and she did her best to keep her knees steady, making sure that her friend had the perfect position to claim her. “If...If you want a baby, then...then do it!”

The journey to find Ash and rediscover their friendship had taken Serena down an unusual path, but as her old friend continued to hammer away she had no regrets. Ash’s outlook on the outside world was one she had been sharing, and perhaps even the thing that had made her seek out her old friend in the first place. The world of Pokémon was too wide and glorious to waste her time in an apartment in Lumiose City! In that heated moment with her body quivering in pleasure, she could think of nothing she wanted more than to be bred by Ash and to stay in his secluded paradise, discovering the same clarity he so clearly had.

When Serena hit her peak it was intense and glorious, the girl’s eyes rolling back into her head and her senses erupting in a burst of pleasure. It was so intense and violent that Ash couldn’t hold back under the weight of it, and the girl’s pussy shuddering and spasming around his cock made it impossible to resist. He hilted himself with one last thrust, determined to make good on his word as his cock began to release spurt after spurt within her. Serena’s eyes snapped open on realization, her head swimming and her orgasmic aftermath still quivering through her, and she simply groaned a joyful noise as she felt her pussy flood with Ash’s cum.

There was so much of it she could barely contain it all, and sure enough as she bent forward she could see large drops of it crashing to the ground between her legs. Once more her knees trembled and threatened giving out underneath her, but thankfully by that point Ash’s grip around her waist was tight and intense. It was just the thing to keep her standing by the time his cock finished filling her up, and he pulled at her soft, clean hair once more to pull her into a standing position.

Without words, Ash kept his cock inside of his old friend from behind, and her head turned back just far enough for their lips to lock once more. While it happened, Ash’s hand slid across Serena’s shoulder, down one of her breasts, and silently moved over the smooth, sensitive flesh of her belly.

And in response, Serena only whimpered in loyal delight. If Ash hadn’t bred her that first time in the woods, she was sure there were going to be many more chances in the future.

***

It was nearly two hours later that the two friends, both sticky with a layer of sweat and tired out from a marathon session of lovemaking, made their way through the woods once more. This time they were heading in a direction Ash had chosen, moving to a stream that he used for cleaning every day. As the two naked friends walked they moved hand-in-hand, and Serena’s voice was gentle and sweet while she spoke.

“I can hardly believe we did all that.” She chuckled, and squeezed Ash’s hand within her own as if to verify one last time that it was all real. “Do...do you think I’m…”

“We’ll find out.” Ash merely smiled, and kept along the path with Serena close in tow. “After we get cleaned up I’ll show you my cabin. I get a visit from Nurse Joy every month, and when she stops by maybe she can tell you.”

“A Nurse Joy?” Serena asked with a giggle, and quirked a brow as she regarded Ash’s nude state once more. “Do you put on clothes for her?”

“Why would I?” Ash beamed, just as the stream came into sight. He started to pick up the pace, pulling Serena right along with him as he did so. “She always has plenty of fun when she visits, just like you did!”

Those words came as a surprise to Serena as they made their way to the stream, but she wasn’t jealous. After all, Ash was alone in the middle of nowhere...knowing that he had monthly visits from a horny Nurse Joy somehow made her feel even better about things. At least the friend she cared so much for hadn’t been going all this time without any fun!

And yet, as they sunk into the water of the stream and pulled themselves close once more, Serena shivered with excitement as she pressed against Ash’s wet, naked body. She had already wildly and recklessly made the decision to join her friend in paradise and willingly become his loyal lover for breeding and pleasure, but the decorated Pokémon trainer was a worldwide celebrity and very, very sought after.

Surely...Serena and a wandering Nurse Joy weren’t the only ones ready to eager to be Ash Ketchum’s companions. He’d always be a Pokemon trainer...but soon, he’d also be a Daddy several times over.

End of Chapter One.


	2. Chapter 2

**Summary for the Chapter:**

> Another old friend has started the search for Ash, and sure enough, she's gonna find him! It's time to see what Lillie thinks of Ash's new lifestyle!

The Kanto Region Master  
Chapter Two  
-by Drace Domino

In the years since their own respective adventures with Ash ended, Serena had made friends with many of the other girls that he used to know. She was frequent pen pals with Dawn, Iris, and May, and even once dropped a line to Jessie just to see if she was interested in joining the club of “girls that once knew the world’s best Pokemon master.” Jessie...wasn’t interested, but Lillie was! The two had become fast friends over a short amount of time, and when Serena set out to find their old mutual friend she had made sure to let Lillie know just where she was going.

And then, two weeks later, another letter arrived addressed to Lillie talking about how happy she was. She had found Ash and he had shown her an entire new way of life, and together they were having the time of their lives as they enjoyed nature, each other, and the thrill of raising Pokemon! As Lillie read the letter that had gone into particular detail about the sort of things that Serena and Ash had been doing, her cheeks had puffed out and a pouty face emerged that she hadn’t worn in quite some time. She was jealous...more so than she’d want to admit. But thankfully, at the very end of Serena’s letter there were a few lines of directions, complete with a short message written in Serena’s cute shorthand.

“Come visit us soon, Lillie!” Lillie’s mouth moved along with the words as she read it, her eyes widening at the ramifications. “Ash says he was always really fond of you, and he’d love for you to join us!”

And Lillie, despite being a grown adult with her own fledgling career and a beautiful apartment in Hau’oli City, found herself feeling the urge to go on a Pokemon adventure just like the old days. An adventure to a region far away from her own - to a whole new part of the world where her new friend Serena and her old friend Ash were waiting for her to join them.

 

“...ahh…” It was another two full weeks before Lillie was on the path in Kanto, following the directions that Serena had included. It had taken her some time to get her affairs in order and let everyone know she’d be gone for a while; but even though they didn’t entirely understand why she was leaving, nobody had tried to stop her. And now the young lady slid her naked body into a cool lake near the end of the evening, drawing in the sounds and the sights of the whole new region.

She had been in Kanto only for a single day, but had already been rather charmed by it. The place was temperate and calm, the Pokemon were friendly and well cared for, and the path was easy to traverse. Part of her had been a bit worried about hitting the road again after so many years of comfort, but her feet didn’t hurt too bad and the cool water of the lake was a nice way to unwind after her first day’s travel. With her long, sweeping blonde hair soaked and her elegant, slender figure slinking down until the water rose up to her shoulders, Lillie closed her eyes and took a deep and content breath, pondering just what would come next.

And thankfully, because the deep forests of Kanto were well-watched, she didn’t have to think too far ahead.

“There you are.” Ash’s voice sounded slightly different from the old days; a bit deeper and more mature, but still ringing with his kind nature. When Lillie opened up her eyes she saw her old friend standing at the edge of the lake, wearing nothing more than a Pidgey on his forearm and a treat pouch connected to a belt around his waist. Ash smiled as he fished one of the treats out and tossed it up into the air, watching as Pidgey dashed off to claim it. “Thanks for letting me know she was here, Pidgey! You’re the best!”

“A...Ash!” Lillie didn’t even watch as Pidgey nipped the treat out of the air and swiftly darted back into the trees to enjoy it; her attention instead focused on the fact that Ash was naked before her. Her eyes instantly trailed down to take a long and lingering look at his cock hanging between his legs, and her cheeks went bright red at the sight of it. Serena wasn’t lying - it was everything she had been promised! The blushing young woman forced her eyes up to her old friend’s face, though had a clearly difficult time collecting her thoughts as she spoke. “You...uh...well, I was...in the area...uh...and I was dirty, so...lake…”

“You don’t have to be shy, Lillie. I’m just happy to see you again.” Ash beamed, and took the time to unclip his treat belt before tossing it to the side. Instantly he slipped down into the water and made his way to his old friend, bringing their naked bodies together as he gave her a big, warm, inviting hug. Even though they were both stripped down to nothing the embrace was purely platonic; or at the very least, not overtly sexual. Even Lillie found the strength to hug Ash back in that moment, though she was a bit more aware about the fact that his cock was pressed in between their bellies as it happened. When they pulled back Ash continued to hold Lillie by her shoulders, looking her up and down with a smile even though everything below her neckline was shrouded by the water. “Wow, Lillie, you...you look amazing! You look-”

“-just like my mother, I know.” Lillie responded sourly, and gave that same big, childish pout that had never quite left her. She even kicked idly at the water, her shoulders slumping as she spoke. “Everyone says I look just like her. It’s all I ever hear.”

“I wasn’t going to say that.” Ash blinked; his head tilting as he regarded his old friend. “I mean, don’t get me wrong, Lusamine is beautiful, but...you’re in a whole different class! But I always knew you were going to grow up as pretty as they come. Heck, you were already there when we went on our Pokemon adventure together.”

In truth, Lillie really did look a lot like Lusamine. She had grown into the same figure as her mother and the same face, and anyone would’ve been able to look at the pair and know they were related. Still, Lillie had her own style and her own mannerisms, and though she was certainly pretty she wasn’t quite as graceful and collected as Lusamine was. ...not that it was an insult, of course. There was a clear, enjoyable charm to Lillie being the cute, sweet, pouty girl she always was even if it was within the frame of a knockout blonde.

Either way, the praise seemed to make her cheeks go all the more red. As the stepped away from each other within the lake both of them found a smooth rock to sit on; Ash dropping down on his rump and Lillie taking a seat not far away. Still enjoying the comfortable water, Lillie found herself once more trying to steal glances at Ash’s length through the haze, but ultimately gave up so she could focus on her friend’s face. Finally she spoke in a sweet voice, though with a clear level of shyness riding across it.

“Serena...tells me that you’ve dedicated yourself to raising Pokemon out here in the wilds of Kanto?” She asked, politely. Even her hands were folded across her lap in the most delicate of fashions, keeping her refined and poised even though she was sitting naked in a lake. “And that the two of you have become intimate with each other?”

“Serena and I have sex all the time, if that’s what you’re asking.” Ash grinned, and though his voice sounded like bragging, Lillie knew better. For all of Ash’s accomplishments he was never really the bragging type - merely enthusiastic for all the good things in his life. He had always been someone that wanted to spread that joy to as many people as possible. “But I’m not just into raising Pokemon. I mean, don’t get me wrong, I’ll always do it! I love Pokemon and want to see them as happy as they can be, but...ever since Serena showed up?” He couldn’t help but grin, looking a bit mischievous as he continued. “Well, I’m starting a family, Lillie! I already got Serena pregnant, and Officer Jenny, too! Jenny doesn’t live with us, though, she’s got too many duties.”

Lillie, wide-eyed, just stared at Ash in response. The casual reveal that he had not one; but two separate women pregnant came as a true surprise to the girl, and her heart rapidly began to race. Serena hadn’t mentioned that part!

“I...I see! I’m very happy for you, Ash.” Lillie responded with a smile, and even stretched a hand out of the water to gently touch his shoulder. “In Serena’s letter, she said I...that I should...uh…”

“That you should join us?” Ash beamed, and offered the girl two big thumbs up, lifting his hands out of the water. “It was her idea, but it’s a great one! We’ll have so much fun together, Lillie! Living out here is the best thing I ever did, and now that Serena moved in it’s even better! We don’t ever wear clothes, and every morning and every evening we just fuck and fuck until we can’t go anymore!”

“She...she mentioned that part.” Lillie coughed softly, her blush intensifying. She was a bit of a timid girl on so many levels; and it had only been Ash’s influence on her that had really helped her come out of her shell to begin with. Now, sitting naked in a lake a few feet away from an old, beloved friend, she felt herself coming out of yet another shell. Serena’s letter had gone into great detail about all the fun she and Ash enjoyed together, and Lillie was sick of being jealous. She wanted to share in some of the happiness, and she wanted to share Ash with her new friend Serena. And since the invitation had already been made, it was clear there was no jealousy anywhere on the table.

Serena had invited her for this purpose - an invitation to be another one of Ash’s pregnant girlfriends in the woods. And Lillie found herself deeply compelled to accept.

“Then...shall we?” Lillie bit down on her bottom lip, nibbling it softly as she waiting for Ash to make his advance. “I really have missed you, Ash.”

“You don’t know the half of it.” Ash replied with a big, wide smile, just as he crept closer to the girl and moved his arms around her once more. “Let me show you everything else you’ve been missing!”

***

Lillie’s cheeks had been solid red ever since she saw Ash’s cock hanging out, and that certainly didn’t seem like it was going to change anytime soon. Especially now as she moved to straddle her old friend, slipping up onto his lap as he continued to lean back within the lake. Ash’s hands had moved to delicately hold her waist and keep her steady as she pulled herself into position, and when she first lowered herself she did so in such a fashion that he wasn’t inside of her - yet. Instead, Ash’s throbbing length was pressed against his belly with Lillie resting her pussy atop it, and though the lake dulled the sensation to some extent it was still quite a bit for the young woman to handle. With her palms moving to grip Ash’s shoulders she looked at her old friend with a slightly nervous expression, very nearly falling into her classic pout as she got herself comfortable.

“This...I never thought I’d be doing this with you, Ash.” She admitted, though it certainly didn’t stop her from rocking back and forth, letting her folds smear up and down across his length. She was intensely warm and already hungry for Ash’s length, though the shy girl within her was still controlling her motions for the most part. Even having her tiny bust exposed to Ash was a bit embarrassing, but there was no hiding the perky little mounds and the large, stiff, sensitive nipples. She did her best to collect her bravery as she studied Ash’s features once more, and let her hands slide from his shoulders down to his smooth, firm chest. “S...Should we kiss, too? This is definitely new to me, I...uh…”

“We’re here to have fun, Lillie.” Ash beamed, his hands tightening around her waist. He shifted his own hips back just enough to create the space for his cock to swing forward, standing up and lining with Lillie’s tender entrance. He began to ease himself inside gently for the moment; slipping the first few inches into a wonderfully warm embrace as he helped the girl slip slowly down his lap. He took the time to study her face and make sure he wasn’t going too fast or too hard, and only continued when he was sure the girl could handle it. “So yeah, I’d love it if you kissed me. It’ll be pretty awkward if I get you pregnant and we’ve never even kissed, huh?”

Lillie, little more than a blushing bundle of nervous energy, nodded and gave a tiny laugh as she pressed forward. The poor thing’s blonde head was spinning in excitement, still a bit bewildered in how swiftly she had changed the course of her life. Alola was a wonderful place to live, but she had been lonely there for far too long...and never did she feel any joy close to that which she experienced at Ash’s side in the past. Being with him again even in those odd circumstances brought back almost too many joyful memories for her to list, and they all fueled her desire to lean forward, press her chest to Ash’s own, and move their lips together.

By the time they kissed Ash had slipped all the way inside of her, and he let his hands travel down along the girl’s waist to the firm, tiny little rump seated on his lap. His squeeze on her ass was gentle yet possessive - ensuring that he wouldn’t let her slip off until they were both satisfied and delighted. And as Lillie’s tongue swung back and forth against Ash’s own the young man gave a lusty groan of pleasure, just as he started to rock up into Lillie’s lap and bring their parts together.

For a while, Lillie’s time with Ash was tender and doting. Slowly the slender blonde beauty rocked back and forth on Ash’s lap, letting his inches fill her to the base of his shaft and then smoothly glide back out again. The water swirled around them as she rode at a steady pace, and for a girl so inexperienced she was handling the motions just fine. Her soaked blonde hair clung to her shoulders and down her back and her glistening breasts squeezed hard to Ash’s chest; letting her surprisingly sensitive nipples grind over him and making her squirm all the more. Ash could already tell - Lillie was a very receptive and sensitive girl, just like her nature suggested. It was almost enough to make him wonder if her mom was the same sort of shy but eager lover, but thinking about Lusamine was hardly needed considering how much Lillie looked like her.

As Lillie got more comfortable; however, Ash started to pick up the pace. His rear lifted from the smooth rock underneath faster and faster, and each time he pushed forward his cock went into Lillie’s depths with even more intense eagerness. Her little entrance was gripped as tight as it could around his cock and she let little gasps leave her lips throughout their kiss, at least until their mouths parted and she gave a sudden cry of pleasure. Ash had only just started fucking her with urgency and speed and she was already spasming; her tender young body shivering and her walls squeezing about him in wild, sudden grasps. It was clear that she had already found one climax atop her old friend’s cock and Ash knew there’d be many more, though Lillie’s slender body might not be able to keep up the same momentum as before.

While the lovely blonde was still gasping and savoring her aftermath, Ash squeezed her body close to his and stood up from the water. He moved to the embankment leading into the lake and laid Lillie flat against a soft spot of grass, even as he still stood knee-deep in the water with his cock lodged inside of her. Now looming over the girl in a missionary position, Ash scooped up Lillie’s legs and moved them up and over his shoulders, hooking them there as he smiled down to his old friend.

“Get used to that feeling, Lillie.” He beamed, studying her basking, glistening features. “There’s plenty more where that came from!” To prove it, Ash didn’t even hesitate and suddenly fell into hard, intense thrusts. He was fucking his dear friend more wildly now, clutching her knees against his shoulders and driving his cock into her with strength and speed. Lillie’s cute and tiny voice broke out into a sudden joyful cry throughout the woods, and her hands clutched each other at her chest, holding on for dear life as she looked up at her friend.

“Oh, oh Ash…! Ash, it’s so wonderful!” Her head was swimming, and all she could think of was the simple fact that Serena was absolutely right about him, that everything she had boasted about in her letters was spot on. He was thick, he was horny, and he was making her feel things that she had never known before. Her tiny little pussy was already shivering again and on the edge of yet another climax, but this time she did her best to hold on as she bounced back and forth against the grass. Her toes curled, her back arched, her throat tightened, and waves of heat and pleasure crashed over her again and again in increasing intensity. All of it watched over by the face of her old friend, a kind smile on his face while he fucked her rough, wet, and hard.

Never did she think a life with Ash in the woods, well-fucked and pregnant and happy, would be her future...but it was hard to argue with the proof of it looming over her. When she found herself unable to stop her second intense orgasm this time she let her voice rise even higher and louder into the air, her entire lower half spasming as she enjoyed a thrashing climax atop his cock. Her hands locked against Ash’s wrists throughout the entire thing, nails digging in against his flesh as if silently begging him to keep at it - to keep fucking her as hard and as fast as he could.

Not that Ash needed any instruction in that area. The water danced around his knees as he continued thrusting forward, slamming his hips to Lillie’s lap again and again and again as she rode out her climax. Lillie’s adorable features were glazed over with a look of lust at that point; her mouth hanging open and her eyes distantly staring up at the sky, her blonde locks and tiny breasts bouncing with every thrust. The pouty sweetheart was enjoying their time together immensely, and Ash shuddered as he felt his own climax rushing through him. A tremble in his thighs, a tightening of his hands around Lillie’s legs, and he thrust himself forward with one last push that clapped their flesh together in a loud, striking fashion. His cock wedged deep into Lillie’s folds as he began to unleash his torrent, releasing spurt after spurt of rich, virile cream into the girl’s tender pussy.

“S...So...so warm...it’s...so warm…” Lillie merely continued to twitch and spasm as she was filled, her toes curling once more as it flooded her. With the chill of the outside air dashing over her soaked body, the warm release of Ash’s cum pumping into her was all the more enjoyable. Enough to bring a warmth to her thighs, her folds, and her belly...enough to remind her of how happy Serena was to boast about her own pregnancy. Would she really be the same as her pen pal? Bred and naked and living in the woods in a constant state of bliss?

Hau’oli City was nice, but...it definitely couldn’t compare to this!

Ash grinned as wide as he could manage as his cock continued to release his torrent, pumping load after load into his friend as he gazed down at her. When he was finally finished he allowed his dick to still rest inside of her, savoring how extra warm she felt now that she was pumped full of cream to the point of overflow. After a few long, deep breaths he allowed her legs to fall from his shoulders and began to pull back, carefully removing his length from his friend’s pussy so he didn’t overstimulate her clearly sensitive body. And with that, the Pokemon master moved to join her against the grass; laying back and staring up at the sky with the same glowing, joyful smile on his face.

“When you catch your breath, we’ll go home and see Serena.” He announced, which made Lillie blush all the harder at the implications. “I’m sure she’ll be excited to see you, and we can all have some fun together! And I think Nurse Joy is scheduled to drop by this week, too!”

“Ash, you’ve...you’ve really made a life for yourself out here, haven’t you?” Lillie couldn’t help but giggle, turning her head to the side so she could study him intimately. One hand even lifted and she guided her fingers across his cheek, the face of the young man that would most certainly father her children. “I’m proud of you. And I’m excited to become a part of it.”

“I’m really happy you’re here.” Ash snatched his old friend’s hand up and brought it to his lips, giving it a small and affectionate kiss before turning his head to the side so he could look right back at her. Afterwards his fingers interlocked with Lillie’s own and he gave her a little squeeze; a reminder of the affection he had for the girl he hadn’t seen in so long. “I’m sure the others will love it, too!”

“The others?” Lillie blinked, curiosity crossing her face. “You mean there’s more coming other than just me and Serena and Jenny and Joy?”

“Oh, for sure!” Ash grinned, and his cock twitched in excitement at the mere thought. “Serena made sure to send out letters to all the others! Dawn and May and Misty and everyone! And if they want to join us here to live and enjoy each other and raise a family, that’s great! And if not?” He shrugged, and gave the same sweet expression he used to back in the old days. “Well, can’t win ‘em all, I suppose! But we’re gonna have a great family no matter what!”

Lillie couldn’t help but smile at his words, and she pulled a little closer towards her new lover. Cum leaked from her overflowing slit and yet she still felt wonderfully warm; especially with the assurance that she and Serena wouldn’t be the only girls to join Ash at his cabin. She had gone from a lonely life to one that was soon to be filled with friends and family - and she was quite happy to be a part of it.

The “girls that once knew the world’s best Pokemon master” club was rapidly becoming the “girls that got knocked up by the world’s best Pokemon master” club, and Lillie was proud to be one of its earliest members!

End of Chapter Two.

**Author's Note:**

> Hope you enjoyed! If you did, please [follow me on tumblr!](http://dracedomino.tumblr.com)


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